Sports It’s been 50+ years since first woman rode in Kentucky Derby. Why are female jockeys still rare? April 22, 2022 Jon Hale, Louisville Courier Journal Comments Off on It’s been 50+ years since first woman rode in Kentucky Derby. Why are female jockeys still rare? It has been eight years since a woman rode in the Kentucky Derby. The first woman to ride in the Derby thinks more female jockeys can find success.